Water → HCID 118221098, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of (R)-(3-((tert-butoxycarbonyl)amino)-4-((3,4-dimethoxybenzyl)amino)-4-oxobutyl)dimethylsulfonium, iodide salt (2 g, 3.7 mmol) in THF (50 mL) was added LHMDS (3.7 mL, 3.7 mmol) dropwise. The reaction was stirred at 0° C. for a further 2 hrs. Then was added saturated ammonium chloride solution and water. The mixture was extracted with 100 mL ethyl acetate. The layers were separated and the organic fraction was washed with water and brine. It was then dried over sodium sulfate, filtered, and evaporated. The residue was purified via silica gel chromatography using 50% ethyl acetate/petroleum ether. Yield 0.8 gms (R)-tert-butyl(1-(3,4-dimethoxybenzyl)-2-oxopyrrolidin-3-yl)carbamate. LCMS (method P) RT 0.82 min, m/z 351.2 (MH+); 1H NMR (400 MHz, chloroform-d) δ 1.45 (s, 9H), 1.78-1.86 (m, 1H), 2.57-2.60 (br s, 1H), 3.15-3.23 (m, 2H), 3.68 (s, 6H), 4.12-4.25 (br s, 1H), 4.40 (m, 2H), 5.14 (br s, 1H), 6.75-6.82 (m, 3H).

Provenance & Evidence